Synthesis of α-substituted β-amino acids via the Ni(II) complex through the Suzuki coupling reaction

doi:10.5246/jcps.2012.06.071

Abstract

CLC Number:

R916

Supporting:

Li Lv, Jiang Wang, Xiao Ding1, Daizong Lin1, Linxiang Zhao2, Hualiang Jiang, Hong Liu^* . Synthesis of α-substituted β-amino acids via the Ni(II) complex through the Suzuki coupling reaction [J]. , DOI: 10.5246/jcps.2012.06.071.

References

[1] (a) Crews, P.; Manes, L.V.; Boehler, M. Tetrahedron Lett. 1986, 27, 2797-2800; (b) Shinagawa, S.; Kanamaru, T.; Harada, S.; Asai, M.; Okazaki, H. J. Med. Chem. 1987, 30, 1458-1463; (c) Namikoshi, M.; Rinehart, K.L.; Dahlem, A.M.; Beasley, V.R.; Carmichael, W.W. Tetrahedron Lett. 1989, 30, 4349-4352; (d) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56, 6523-6527; (e) Roers, R.; Verdine, G.L. Tetrahedron Lett. 2001, 42, 3563-3565.
[2] Chen, D.Z.; Patel, D.V.; Hackbarth, C.J.; Wang, W.; Dreyer, G.; Young, D.C.; Margolis, P.S.; Wu, C. Ni, Z.J.; Trias, J.; White, R.J.; Yuan, Z.Y. Biochemistry. 2000, 39, 1256-1262.
[3] Clements, J.M.; Beckett, R.P.; Brown, A.; Catlin, G.; Lobell, M.; Palan, S.; Thomas, W.; Whittaker, M.; Wood, S.; Salama, S.; Baker, P.J.; Rodgers, H.F.; Barynin, V.; Rice, D.W.; Hunter, M.G. Antimicrob. Agents Chemother. 2001, 45, 563-570.
[4] (a) Fitzi, R.; Seebach, D. Tetrahedron. 1988, 44, 5277-5292; (b) Evans, D.A.; Britton, T.C.; Ellman, J.A.; Dorow, R.L. J. Am. Chem. Soc. 1990, 112, 4011-4030; (c) Danho, W.; Tilley, J.W.; Shiuey, S.J.; Kulesha, I.; Swistok, J.; Makofske, R.; Michalewsky, J.; Wagner, R.; Triscari, J.; Nelson, D.; Chiruzzo, F.Y.; Weatherford, S. Int. J. Peptide Protein Res. 1992, 39, 337-347; (d) Shapiro, G.; Buechler, D.; Marzi, M.; Schmidt, K.; Gomezlor, B. J. Org. Chem. 1995, 60, 4978-4979; (e) Davis, F.A.; Liang, C.H.; Liu, H. J. Org. Chem. 1997, 62, 3796-3797; (f) Belokon, Y.N.; Kochetkov, K.A.; Churkina, T.D.; Ikonnikov, N.S.; Chesnokov, A.A.; Larionov, O.V.; Kagan, H.V. Russ. Chem. Bull. 1999, 48, 917-923.
[5] Qiu, W.; Soloshonok, V.A.; Cai, C.; Tang, X.; Hruby, V.J. Tetrahedron. 2000, 56, 2577-2582.
[6] (a) Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983-1004; (b) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1, 1-15; (c) Liu, M.; Sibi, M.P. Tetrahedron. 2002, 58, 7991-8035.

[7] Sewald, N. Amino Acids. 1996, 11, 397-408.
[8] (a) Davies, S.G.; Ichihara, O. Tetrahedron: Asymmetry. 1991, 2, 183-186; (b) Davies, S.G.; Ichihara, O.; Walters, I.A.S. J. Chem. Soc. Perkin Trans I. 1994, 1, 1141-1147.
[9] (a) Sewald, N.; Hiller, K.D.; Helmreich, B. Liebigs Ann. Chem. 1995, 925-928; (b) Sewald, N.; Hiller, K.D.; Korner, M.; Findeisen, M. J. Org. Chem. 1998, 63, 7263-7274.
[10] (a) Cardillo, G.; Tolomelli, A.; Tomasini, C. J. Org. Chem. 1996, 61, 8651-8654; (b) Soloshonok, V.A.; Svedas, V.K.; Kukhar, V.P.; Kirilenko, A.G.; Rybakova, A.V.; Solodenko, V.A.; Fokina, N.A.; Kogut, O.V.; Galaev, I.Y.; Kozlova, E.V.; Shishkina, I.P.; Galushko, S.V. Synlett. 1993, 339-341; (c) Soloshonok, V.A.; Kirilenko, A.G.; Fokina, N.A.; Galushko, S.V.; Kukhar, V.P.; Svedas, V.K.; Resnati, G. Tetrahedron: Asymmetry. 1994, 5, 1225-1228; (d) Soloshonok, V.A.; Soloshonok, I.V.; Kukhar, V.P.; Svedas, V.K. J. Org. Chem. 1998, 63, 1878-1884.
[11] Bardou, A.; Célérier, J.P.; Lhommet, G. Tetrahedron Lett. 1997, 38, 8507-8510.
[12] Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas III., C.F. J. Am. Chem. Soc. 2002, 124, 1866-1867.
[13] (a) Tararov, V.I.; Saveleva, T.F.; Kuznetsov, N.Y.; Ikonnikov, N.S.; Orlova, S.A.; Belokon, Y.N.; North, M. Tetrahedron: Asymmetry. 1997, 8, 79-83; (b) Xu, P.F.; Chen, Y.S.; Lin, S.I.; Lu, T.J. J. Org. Chem. 2002, 67, 2309-2314.
[14] Yang, H.; Foster, K.; Stephenson, C.R.J.; Brown, W.; Roberts, E. Org. Lett. 2000, 2, 2177-2179.

[15] Cimarelli, C.; Palmieri, G. J. Org. Chem. 1996, 61, 5557-5563.
[16] Belokon, Y.N.; Maleyev, V.I.; Vitt, S.V.; Ryzhov, M.G.; Kondrashov, Y.D.; Golubev, S.N.; Vauchskii, Y.P.; Kazika, A.I.; Novikova, M.I.; Krasutskii, P.A.; Yurchenko, A.G.; Dubchak, I.L.; Shklover, V.E.; Struchkov, Y.T.; Bakhmutov, V.I.; Belikov, V.M. J. Chem. Soc. Dalton Trans. 1985, 17-26.
[17] (a) Belokon, Y.N.; Sagyan, A.S.; Djamgaryan, S.A.; Bakhmutov, V.I.; Vitt, S.V.; Batsanov, A.S.; Struchkov, Y.T.; Belikov, V.M. J. Chem. Soc. Perkin. Trans. I. 1990, 2301-2310; (b) Soloshonok, V.A.; Avilov, D.V.; Kukhar, V.P.; Meervelt, L.V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671-4674; (c) Soloshonok, V.A.; Tang, X.J.; Hruby, V.J.; van Meervelt, L. Org. Lett. 2001, 3, 341-343; (d) Soloshonok, V.A.; Ohkura, H.; Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yamazaki, T. Tetrahedron Lett. 2002, 43, 5445-5448; (e) Soloshonok, V.A.; Cai, C.Z.; Yamada, T.; Ueki, H.; Ohfune, Y.; Hruby, V.J. J. Am. Chem. Soc. 2005, 127, 15296-15303; (f) Sorochinsky, A.; Voloshin, N.; Markovsky, A.; Belik, M.; Yasuda, N.; Uekusa, H.; Ono, T.; Berbasov, D.O.; Soloshonok, V.A. J. Org. Chem. 2003, 68, 7448-7454.
[18] (a) Deng, G.H.; Wang, J.; Zhou, Y.; Jiang, H.; Liu, H. J. Org. Chem. 2007, 72, 8932-8934; (b) Wang, J.; Shi, T.; Deng, G.; Jiang, H.; Liu, H. J. Org. Chem. 2008, 73, 8563-8570; (c) Wang, J.; Shi, J.M.; Zhang, X.D.; Lin, D.Z; Jiang, H.L.; Liu, H. Synthesis. 2009, 1744-1752; (d) Ding, X.; Ye, D.J.; Liu, F.; Deng, G.H.; Liu, G.N.; Luo, X.M.; Jiang, H.L.; Liu, H. J. Org. Chem. 2009, 74, 5656-5659; (e) Lin, D.Z.; Deng, G.H.; Wang, J.; Ding, X.; Jiang, H.L.; Liu, H. J. Org. Chem. 2010, 75, 1717-1722.